Trifluoroacetic anhydride → 2-Chloro-5-(trifluoromethyl)pyridine 1-oxide
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][N:3]=1.NC(N)=[O:14].OO.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:9])([F:10])[F:11])=[CH:4][N+:3]=1[O-:14]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
2-Chloro-5-trifluoromethyl-pyridine (16, 10 mmol) was dissolved in CH2Cl2 (20 mL) and UHP (Urea-hydrogen peroxide addition compound, 21 mmol) was added. The mixture was cooled to 0° C., trifluoroacetic anhydride (20 mmol) was then slowly added to the reaction mixture. It was allowed to warm to room temperature and stirred until the reaction was completed judged by TLC. The reaction was quenched with aqueous Na2SO3, stirred for 4 h, washed with saturated aqueous NaHCO3, and dried over anhydrous MgSO4. Column chromatography afforded 1.8 g of compound 17 as oil.
Workup
- additionwas added
- temperatureto warm to room temperature
- customThe reaction was quenched with aqueous Na2SO3
- stirringstirred for 4 h
- washwashed with saturated aqueous NaHCO3
- dry with materialdried over anhydrous MgSO4
Sources & evidence
- ORD record
- ord-a3f42d8db40c4f96964299b8edb84aba
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08084454B2
Reaction notes
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